Cheap Flights to South Side from $32

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How Much Does it Cost To Fly To South Side?

The cheapest prices found with in the last 7 days for return flights were $63 and $32 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
MCOChicagoJuly 2 to July 8$87
FLLChicagoJuly 2 to July 9$87
DENChicagoAugust 15 to August 18$94
IAHChicagoAugust 15 to August 18$94
MSPChicagoAugust 12 to August 18$97
IAHChicagoJuly 21 to July 23$102
PHXChicagoAugust 31 to September 4$104
MSPChicagoAugust 20 to August 23$109
MCOChicagoAugust 8 to August 11$138
LAXChicagoJuly 1 to July 2$141
DENChicagoAugust 11 to August 16$143
PHXChicagoAugust 19 to August 26$154
LAXChicagoAugust 9 to August 12$154
MSYChicagoSeptember 7 to September 8$170
FCOChicagoJune 17 to June 24$785
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DENChicagoJune 14 to June 16$146
ATLChicagoJune 15 to June 18$195
MCOChicagoJune 14 to June 21$220
FLLChicagoJune 13 to June 16$240
LAXChicagoJune 14 to June 20$261
MSYChicagoJune 15 to June 19$266
MCOChicagoJune 15 to June 26$286
DENChicagoJune 14 to June 18$291
MSPChicagoJune 14 to June 15$317
LAXChicagoJune 15 to June 21$318
MSPChicagoJune 15 to June 16$330
MSYChicagoJune 15 to June 17$352
PHXChicagoJune 13 to June 16$357
FLLChicagoJune 15 to June 21$361
FCOChicagoJune 13 to June 29$778
*Prices include taxes and fees

South Side Flight Information

Traveling to
South Side
Lowest Price
$63
Number of Airlines Serving
Airlines Serving
Spirit Airlines
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing South Side Accommodation Deals

Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,003 reviews)
"Quiet and close to good food and bar."

Reviewed on Jun 1, 2025

Chinatown Hotel Chicago
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,062 reviews)
"The hotel was very clean, right in the middle of Chinatown, and we felt extremely safe walking around. You can park in a lot about 2 blocks away that is $18.99 for 24 hours. My mom left a shirt there, and they called and asked if we wanted it back. There is no breakfast, but there is a Starbucks ..."

Reviewed on Jun 9, 2025

Jaslin Hotel
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,508 reviews)
"The restaurant was good the room was clean"

Reviewed on Jun 8, 2025

Best Western Grant Park Hotel
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Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,003 reviews)
"Everything’s was great. Just the shwets are"

Reviewed on Jun 8, 2025

Hyatt Regency McCormick Place Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in South Side

The Wheeler Mansion

The Wheeler Mansion

4 out of 5
2020 South Calumet Avenue, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
The Wheeler Mansion
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,508 reviews)
"The restaurant was good the room was clean"

Reviewed on Jun 8, 2025

Best Western Grant Park Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,003 reviews)
"Everything’s was great. Just the shwets are"

Reviewed on Jun 8, 2025

Hyatt Regency McCormick Place Chicago
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,003 reviews)
"Quiet and close to good food and bar."

Reviewed on Jun 1, 2025

Chinatown Hotel Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in South Side

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,003 reviews)
"Everything’s was great. Just the shwets are"

Reviewed on Jun 8, 2025

Hyatt Regency McCormick Place Chicago
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,508 reviews)
"The restaurant was good the room was clean"

Reviewed on Jun 8, 2025

Best Western Grant Park Hotel
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,062 reviews)
"The hotel was very clean, right in the middle of Chinatown, and we felt extremely safe walking around. You can park in a lot about 2 blocks away that is $18.99 for 24 hours. My mom left a shirt there, and they called and asked if we wanted it back. There is no breakfast, but there is a Starbucks ..."

Reviewed on Jun 9, 2025

Jaslin Hotel
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago

Marriott Marquis Chicago

4 out of 5
2121 South Prairie Avenue, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
9.2/10 Wonderful! (1,002 reviews)
"Staff helped to change from 1 bed to 2"

Reviewed on Jun 7, 2025

Marriott Marquis Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best South Side Flight and Hotel Packages

South Side flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Trump International Hotel & Tower Chicago
Nobu Hotel Chicago
Don't see what you're looking for?
See all available trips from Dallas to South Side
View all trips

South Side flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Downtown South Loop
Don't see what you're looking for?
See all available trips from Philadelphia to South Side
View all trips

Need a Car For After Your Flight?

Lowest prices found within the past 8 hours. Prices and availability subject to change. Additional terms may apply.

Plane Tickets To South Side

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to South Side. Browse through our inventory to explore a wide range of cheap flights to South Side to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in South Side as you anxiously await to exit the plane and explore what South Side has to offer. Considering all the amazing local food and culture in South Side, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to South Side to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to South Side without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to South Side with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to South Side today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.